Cyclopentanecarboxylic acid is an organic compound with the formula C5H9CO2H. It is a colorless nonvolatile oil. It can be produced by the palladium-catalyzed hydrocarboxylation of cyclopentene:[2]
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3D model (JSmol)
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| ECHA InfoCard | 100.020.245 |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C6H10O2 | |
| Molar mass | 114.144 g·mol−1 |
| Appearance | colorless oil |
| Density | 1.0510 g/cm3 |
| Melting point | −7 °C (19 °F; 266 K) |
| Boiling point | 212 °C (414 °F; 485 K) |
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| GHS labelling:[1] | |
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| H315, H319, H335 | |
| P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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- C5H8 + CO + H2O → C5H9CO2H
An alternative route involves base-induced ring contraction of 2-chlorocyclohexanone to give the ester methyl cyclopentanecarboxylate, which can be hydrolyzed to the carboxylic acid.[3]
References
edit- ^ "Cyclopentanecarboxylic acid". pubchem.ncbi.nlm.nih.gov.
- ^ Sang, Rui; Kucmierczyk, Peter; Dühren, Ricarda; Razzaq, Rauf; Dong, Kaiwu; Liu, Jie; Franke, Robert; Jackstell, Ralf; Beller, Matthias (2019). "Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation". Angewandte Chemie International Edition. 58 (40): 14365–14373. doi:10.1002/anie.201908451. PMID 31390131. S2CID 199466915.
- ^ D. W. Goheen, W. R. Vaughan (1959). "Methyl Cyclopentanecarboxylate". Organic Syntheses. 39: 37. doi:10.15227/orgsyn.039.0037.